H-His-OH

CAS# 71-00-1

H-His-OH

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Chemical structure

H-His-OH

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Chemical Properties of H-His-OH

Cas No. 71-00-1 SDF Download SDF
PubChem ID 6274 Appearance Powder
Formula C6H9N3O2 M.Wt 155.2
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : 30 mg/mL (193.36 mM; Need ultrasonic)
Chemical Name (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
SMILES C1=C(NC=N1)CC(C(=O)O)N
Standard InChIKey HNDVDQJCIGZPNO-YFKPBYRVSA-N
Standard InChI InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of H-His-OH

DescriptionL-Hisidine is an essential amino acid for infants. L-Hisidine is an inhibitor of mitochondrial glutamine transport.In Vitro:L-histidine completely inhibits growth and its effect on viability is inversely related to FLO11 expression. L-histidine does not affect the viability of the Δflo11 and S288c strains. L-histidine dramatically decreases air-liquid biofilm formation and adhesion to polystyrene of the flor yeasts with no effect on the transcription level of the FLO11 gene. Moreover, L-histidine modifies the chitin and glycans content on the cell-wall of flor yeasts[1].In Vivo:L-histidine (100 mg/kg) completely inhibits the brain edema in thioacetamide-treated rats[2]. Histamine release stimulated by high K+ from the hypothalamus in the L-histidine diet group is 60% of that in the control group. However, the concentrations of other monoamines and their metabolites are not changed by the L-histidine diet. The open-field tests show that the L-histidine diet group spends a shorter amount of time in the central zone, and the light/dark box tests demonstrate that the L-histidine diet group spends a shorter amount of time in the light box, suggesting that the L-histidine diet induced anxiety-like behaviors[3].

References:
[1]. Bou Zeidan M, et al. L-histidine inhibits biofilm formation and FLO11-associated phenotypes in Saccharomyces cerevisiae flor yeasts. PLoS One. 2014 Nov 4;9(11):e112141. [2]. Rama Rao KV, et al. Brain edema in acute liver failure: inhibition by L-histidine. Am J Pathol. 2010 Mar;176(3):1400-8. [3]. Yoshikawa T, et al. Insufficient intake of L-histidine reduces brain histamine and causes anxiety-like behaviors in male mice. J Nutr. 2014 Oct;144(10):1637-41.

Protocol

Animal Administration [2][3]
Rats: TAA (300 mg/kg i.p) is given to animals daily for 3 days. L-histidine (100 mg/kg) is dissolved in saline and injected (i.p.) daily 2 hours before each TAA injection. To prevent hypoglycemia and dehydration, rats are given 12.5 ml/kg of fluid therapy (5% dextrose and 0.45% saline with 20 mEq/L of potassium chloride) every 12 hours, s.c. Normal controls receive saline (vehicle used for TAA), whereas another group of rats are given L-histidine alone (100 mg/kg) daily for 3 days. TAA-treated rats are clinically monitored, and stages of encephalopathy are graded[2]. Mice: The control group is fed with the AIN-93G purified diet that contains 5.08 g L-histidine/kg, whereas the L-histidine diet group is fed with AIN-93G that contains 1.28 g L-histidine/kg (25% of the histidine content in AIN-93G). To equalize the total amount of amino acids, glutamine is added to the L-histidine diet to counterbalance the changes in the histidine content (18.32 g L-glutamine/kg AIN-93G vs. 23.72 g L-glutamine/kg L-histidine diet). Both diets are isonitrogenous. At 8 wk of age, the mice are weighed and assigned to 2 different diets. The mice are allowed ad libitum access to water and their respective diets, and they are housed for at least 2 wk in the laboratory before starting the experiments[3].

References:
[1]. Bou Zeidan M, et al. L-histidine inhibits biofilm formation and FLO11-associated phenotypes in Saccharomyces cerevisiae flor yeasts. PLoS One. 2014 Nov 4;9(11):e112141. [2]. Rama Rao KV, et al. Brain edema in acute liver failure: inhibition by L-histidine. Am J Pathol. 2010 Mar;176(3):1400-8. [3]. Yoshikawa T, et al. Insufficient intake of L-histidine reduces brain histamine and causes anxiety-like behaviors in male mice. J Nutr. 2014 Oct;144(10):1637-41.

H-His-OH Dilution Calculator

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H-His-OH Molarity Calculator

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Preparing Stock Solutions of H-His-OH

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4433 mL 32.2165 mL 64.433 mL 128.866 mL 161.0825 mL
5 mM 1.2887 mL 6.4433 mL 12.8866 mL 25.7732 mL 32.2165 mL
10 mM 0.6443 mL 3.2216 mL 6.4433 mL 12.8866 mL 16.1082 mL
50 mM 0.1289 mL 0.6443 mL 1.2887 mL 2.5773 mL 3.2216 mL
100 mM 0.0644 mL 0.3222 mL 0.6443 mL 1.2887 mL 1.6108 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on H-His-OH

Cisplatin-mediated selective hydrolytic cleavage of methionine-containing peptides with neighboring serine or histidine residues.[Pubmed:15522420]

J Inorg Biochem. 2004 Nov;98(11):1947-56.

The pH- and time-dependent reactions of the anticancer drug cisplatin, cis-[PtCl(2)(NH(3))(2)], with the peptides Ac-Gly-Met-Gly-OH, Ac-Ser-Met-OH and Ac-Met-His-OH (Gly=glycyl, Met=methionyl, Ser=seryl, His=histidyl) at 313 K have been investigated by high-performance liquid chromatography, nuclear magnetic resonance and mass spectrometry. In the major equimolar reaction pathway for Ac-Gly-Met-Gly-OH, rapid anchoring at the methionine sulphur (kappaS) is followed by successive metalations of the methionine N(M) and glycyl N(G1) amide nitrogens in N-terminal direction to afford bidentate kappa(2)S,N(M) and tridentate kappa(3)S, N(M),N(G1) complexes. Cleavage of acetic acid at the second upstream amide bond is observed after 10 h leading to slow formation of [Pt(H-Gly-MetH(-1)-Gly-OH-kappa(3)S,N(M),N(G1))(NH(3))](+) at pH<6. [Pt(H-Ser-MetH(-1)-OH-kappa(3)S,N(M),N(S))(NH(3))](+) results from an analogous cisplatin-mediated regioselective hydrolytic cleavage reaction for Ac-Ser-Met-OH in moderately acid solution (pH<4). After passing through a minimum at pH 4.4, the concentration of the cleavage product in the reaction mixture after 500 h increases steadily on raising the pH and release of acetic acid is effectively quantitative for 7pH9.5. A competing mechanism involving nucleophilic attack of the serine side chain on the acetyl function can be inferred for pH>6 by the HPLC detection of a second intermediate kappa(3)S,N(M),N(S) species. In striking contrast, the reaction of cisplatin with Ac-Met-His-OH leads to release of acetylmethionine and formation of a final histidine product cis-[PtCl(H-His-OH-kappa(2)N3,N(H)) (NH(3))](+) at pH<6 by a kappaS-->kappa(2)S, N3-->kappa(3)S, N(H),N3-->kappa(2)N3,N(H)(H-His-OH) pathway.

Description

L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

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